


the one you love from time to time.

by katarama



Category: Teen Wolf (TV)
Genre: Alternate Universe - Escorts, Aromantic, BDSM, M/M, Musician Stiles, No Romance, Punk Stiles Stilinski, Sex, Sex Work, Trans Character, Trans Stiles Stilinski
Language: English
Status: Completed
Published: 2016-06-22
Updated: 2016-06-22
Packaged: 2018-07-16 13:40:21
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,449
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7270537
Author URL: https://archiveofourown.org/users/katarama/pseuds/katarama
Summary: <blockquote class="userstuff">
              <p>Jackson would think that an escort wouldn’t be at the top of the list of trustworthy individuals, not when the tabloids would be thrilled to find out a punk band drummer's filthy, juicy little secrets.  </p>
<p>But Stiles got tipsy and called Lydia, and Lydia sent him Jackson, and suddenly Jackson was checking to make sure a moderately famous musician was sober enough to pay to ride him in a shitty hotel room.</p>
            </blockquote>





	the one you love from time to time.

**Author's Note:**

  * For [alexenglish](https://archiveofourown.org/users/alexenglish/gifts).



“I’ll see you next time.”

It’s Jackson’s favorite thing to say to Stiles.  It’s become routine, now.  Jackson’s smirk as he slides his jeans back on.  The scowl on Stiles’ face, his eyebrows furrowed.  Stiles doesn’t even try to disagree with Jackson.  He used to, once upon a time, used to snap back.  “Don’t think your ass is that great,” or, “Don’t know that your mouth’s good enough to be that cocky.”  

They both know better by now.  They’ve been doing this together every once in a while for going on two years, now.

“Fuck off,” Stiles still says, just for good measure.  There’s no heat to it.  Jackson would know.  Stiles is the kind of person who can say fuck off with some feeling behind it.  Jackson supposes that’s what happens when you’re an aggressively bisexual and openly trans drummer in a punk band; Stiles doesn’t have the arms covered in tattoos, but he has the sharp sarcasm and the deadpan stare down pat, the immediate instinct to distrust.  

Jackson would think that an escort wouldn’t be at the top of the list of trustworthy individuals, not when the tabloids would be thrilled to find out those kinds of filthy, juicy little secrets.  But Stiles got tipsy and called Lydia, and Lydia sent him Jackson, and suddenly Jackson was checking to make sure a moderately famous musician was sober enough to pay to ride him in a shitty hotel room.

“Give me your number,” Stiles had demanded when the night was over.  Jackson could’ve told him to go through the agency, like everyone else has to.  Stiles wasn’t even intimidating.  He was mostly falling asleep.

“Fine,” Jackson said, instead.  Stiles had a fat wallet and a pretty face, and Jackson wasn’t gonna turn down business.  Stiles put the number of Jackson’s burner into his phone and took a picture of Jackson’s dick to set as his contact picture, the picture’s framing crooked and blurry.

“I’ll remember you this way,” Stiles had joked.  

“Just wait until you feel my mouth,” Jackson said.

* * *

 

With regular clients, Jackson likes to draw things out.  Jackson knows he has to put out a certain amount upfront to get people to come back at all, but he likes to give people a little taste at a time, to keep some tricks up his sleeve to keep people coming back for more.  There’s nothing better than surprising a client who thinks they’ve seen everything, their eyes going wide, their thighs shaking.

Stiles, though, makes that incredibly hard.

Jackson is used to demanding clients.  It’s part of the gig, with being more high-end.  Jackson deals with rich businessmen, smarmy and self-aggrandizing and particular.  He knows how to handle them.  Smirking and looking up from under his eyelashes and playing hard to get have all become skills of Jackson’s, because they put the power in his hands early on, put him in a position to tease, to make them wait, unless they’re willing to assert themselves.

Stiles, on the other hand, appears to mostly be cheap as fuck.  Sure, he tips well, and he’s willing to shell out for Jackson.  But he wears shoes that could’ve used replacing three years ago.  He gets shitty motel rooms when he could afford to stay with the band somewhere much nicer.  He always talks like this is going to be the last time, like Jackson has to make his time worth the money.  

It makes it hard for Jackson not to be totally in it.  It makes it hard for Jackson not to need to prove himself, to show Stiles just how amazing he can be, to show him just why Jackson’s time is worth what it is.  Stiles puts it on Jackson right away to impress him, his face wearing that fucking impassive mask that makes Jackson’s gut hot, that Jackson will pull out all the stops to make slip.  

When Jackson succeeds, Stiles is fucking noisy.  He’s noisy and needy and squirmy, and he’ll tell Jackson exactly what he wants, or what he doesn’t, on a given day.  But even that Stiles turns into a challenge, giving as good as he gets, making Jackson draw out every ounce of pleasure to get Stiles’ praise at the end.  Pushing Jackson’s head between his legs and having Jackson suck at his condom-covered, silicon dick until Jackson’s lips are puffy and sore.  Waiting until Jackson’s lost in the feeling of suction, the blissful heaviness on his tongue that has Jackson’s jaw going sore and his head going fuzzy, before finally giving Jackson what he really wants, bucking into Jackson’s mouth and fucking his throat raw.

Jackson gets overwhelmed by it, sometimes.  Stiles’ hand in his hair, sharp tugs that make Jackson moan around his cock.  Stiles using Jackson’s thigh, or fingers, or cock, treating Jackson’s body like a convenient, expensive, tactile sex toy.  Jackson feels like it shouldn’t get him so hard and leaking, especially when there’s so much potential to make him insecure.  Stiles could get this from anyone, could easily smirk and snark and be standoffish to hide how awkward he is and manage to pick up a dude at a party anyway, get close to the same thing, for less.  

But it’d be a lie if Jackson tried to say he wasn’t into it, and Jackson doesn’t generally try to lie about what he likes.  Sure, he takes a little push, sometimes, a firm hand when he’s being a brat.  But Jackson isn’t afraid of liking sex, or being subby, or liking cock.  It turns out that works in his favor.

“I wouldn’t keep coming back if you weren’t such a slut for this,” Stiles tells him.  It should probably feel like an insult, but by this point, it’s a source of pride for Jackson.

“You wouldn’t keep coming back if you weren’t such a slut for this, either,” Jackson says, and from the way Stiles grins, Jackson thinks he gets it, too.

* * *

 

“Do you ever wish I were around more often?” Stiles asks one day when they’re breaking for the night, settling in after a shower to sleep.  Jackson’s brain is running slow, and it’s a tricky question.  He’s not sure how to handle it, immediately.

He thinks about sex with Stiles, sometimes, off hours.  He doesn’t feel bad jerking off on it; he does that with a few of his clients.  Weekends with Stiles, though few and far between, are admittedly some of his favorites, leaving him aching and sore and satisfied.

“You have a job,” Jackson says, “and so do I.  You can’t rent me out all the time.”

“Be the tour sex worker,” Stiles says lightly.  He places his hand on Jackson’s chest, running his fingers along the lines of Jackson’s abs.  “See the country through the windows of a tour bus and nights in hotels.”

“That’s not a real offer, is it?” Jackson asks carefully.  He likes spending weekends with Stiles.  They’re always a nice surprise, an abrupt text and a flurry of rearranging Jackson’s schedule to squeeze Stiles in.  The sex is good.  The pay is good.  Stiles is a dick, sure, but he realizes that Jackson is also a dick, and he doesn’t expect anything different from Jackson.  It’s the most real that Jackson feels on the job, going back and forth with Stiles, calling him a douchebag without having to fret that Stiles will get offended.

But Jackson likes his weekends with Stiles just because they’re that; sporadic weekends, a taste of Stiles without having to commit to Stiles all the time.  They feel spontaneous, like sex vacations, exciting and filthy and hazy from all the orgasms.  He doesn’t want to strangle Stiles for a solid 83% of the time, they both get awesome sex, and Jackson gets a whole weekend’s worth of pay.

“No,” Stiles says.  “I have a job, and so do you.”  His fingers follow the line of Jackson’s body up to his chest, his hand drifting to below Jackson’s nipple, where on his own body there are scars.  “You’re obnoxious.  Best in small doses.”

“Fuck off,” Jackson says lazily.  

He’s relieved, though, more than anything.  Because he and Stiles are on the same page here.  They can have their occasional weekends whenever Stiles rolls into town, and Stiles can send Jackson pictures of his fingers on his dick when Stiles is drunk.  But there are no expectations for more, no Pretty Woman fantasies or heartfelt confessions of misplaced feelings.

“Night,” Stiles says, after both of them have let out the breaths they were holding.  “In the morning I can fuck you in the shower.”

“Sounds perfect,” Jackson says, and he rolls over and prepares to sleep.

**Author's Note:**

> On tumblr [here](http://sleepy-skittles.tumblr.com).


End file.
